Sodium borohydride → (4-Iodopyridin-2-yl)methanol

HRID 1038122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038122
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](OC)=[O:9])[CH:3]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 22742038Methyl 4-iodopicolinate

Produkt 1

HCID 59770929(4-Iodopyridin-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-iodopicolinate 5AN (2.83 g, 10.78 mmol) in MeOH (30 ml) was added NaBH4 (1.59 g, 43.12 mmol) portion wise at 0° C. Reaction mixture was allowed to warm up to r.t. After stirring for 3 days at r.t, it was quenched with, 14 ml of 1N NaOH. Reaction mixture was diluted with DCM (200 ml). The organic layer was washed with water (2×30 ml), dried over MgSO4, filtered and concentrated. The residue was purified on silica gel eluting with 3/1 EtOAc/Hexane to give the desired product (4-iodo-pyridin-2-yl)-methanol 6AN (2.27 g, 90%).

Aufarbeitung

  1. customReaction mixture
  2. customwas quenched with, 14 ml of 1N NaOH
  3. customReaction mixture
  4. washThe organic layer was washed with water (2×30 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel eluting with 3/1 EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-5fff4d3cd6ee422e965963eb72d65335
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546404B2

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